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1,3-Bis(carboxymethyl)imidazolium Chloride as a Metal-Free and Recyclable Catalyst for the Synthesis of N-Allylanilines by Allylic Substitution of Alcohols

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The 1,3-bis(carboxymethyl)imidazolium chloride, which is easily and in a straightforward manner prepared readily from starting materials in multigram scale, is employed as catalyst in the synthesis of N-allylanilines by allylic… Click to show full abstract

The 1,3-bis(carboxymethyl)imidazolium chloride, which is easily and in a straightforward manner prepared readily from starting materials in multigram scale, is employed as catalyst in the synthesis of N-allylanilines by allylic substitution of alcohols with anilines. This metal-free catalyst allows the reaction to be carried out under mild reaction conditions (80 °C and air open vessel) and proved to be efficient for a diversity of anilines and allylic alcohols, providing exclusively the product of N-substitution independently of the substituents in the aniline reactant. The process described is simple and effective, allowing N-allylanilines to be obtained in preparative scale [e.g., 3.30 g of N-(1,3-diphenylallyl)-4-nitroaniline]. The catalyst could be reused up to 15 cycles without loss of activity, proving its robustness.

Keywords: catalyst synthesis; carboxymethyl imidazolium; bis carboxymethyl; substitution; catalyst; imidazolium chloride

Journal Title: ACS Sustainable Chemistry & Engineering
Year Published: 2018

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